A 6H-benzo [c] chromene-6-one derivative has been known as an intermediate product of a 1,2-dihydroquinoline derivative having glucocorticoid receptor binding activities (for example, see WO2007/032556 (PTD 1)). In addition, the derivative has also been known as a selective estrogen β receptor agonist (see, for example, Bioorganic & Medicinal Chemistry Letters, 16, 2006, 1468-1472 (NPD 1)). NPD 1 describes a method of obtaining a 3-hydroxy-6H-benzo [c] chromene-6-one derivative by causing two equivalents of resorcinol and a bromobenzoic acid derivative to react in water at 100° C. in the presence of two equivalents of sodium hydroxide and a catalyst quantity of copper sulfate.
When the present inventors attempted to manufacture a 3-hydroxy-6H-benzo [c] chromene-6-one derivative with the method described in NPD 1, however, a large amount of by-product was generated, the derivative could not be manufactured at satisfactory yield, and improvement in yield from a point of view of industrial manufacturing was required. For example, in a case where 2-bromobenzoic acid of which position 3 or position 5 was substituted with a nitro group which is an electron-withdrawing group was employed as a bromobenzoic acid derivative, aromatic substitution reaction to a bromo group by a hydroxy group of water or resorcinol proceeded and a target compound could be manufactured only at yield around 10% or less.